Paramethyl parahydroxy diphenyl sulphide and method of preparing the same



Patented Aug. 20, 1935 PARAMETHYL PARAHYDROXY DIPHENYL.

SULPHIDE AND MET THE SAME Treat B. Johnson, Beth Incorporated,

Sharp & Dohme,

HOD OF PREPARING any, Conn, assignor to Philadelphia,

Pa., a corporation of Maryland No Drawing.

Original application March 10, 1928, Serial No. 260,817.

Divided and this application January 12, 1934, Serial No. 706,408

2 Claims.

This invention relates to a new derivative of hydroxydiphenyl sulphide, namely, the paramethyl parahydroxy diphenyl sulphide, and to a process of preparing the same. a

This application is a division of my prior application Serial No. 260,817, now Patent No. 1,976,732 of October 16, 1934.

The production of the new compound is illustrated by the following example, the parts being by weight.

ExampZe.- parts of para-anisidine (1.25 mols.) are dissolved in 85 parts of concentrated hydrochloric acid (2.5 mols.) and the solution diluted with Water. The amine is then diazotized as usual. 53 parts of sodium para thiocresolate (1 mol.) are dissolved in 100 parts of water containing 13 parts of sodium hydroxide and the solution heated to C. The prepared diazo solution is slowly added to this heated solution, with agitation to insure intimate contact and uniform distribution and reaction. Under these conditions coupling takes place with decomposition of the intermediate diazo-thio-ether and formation of paramethyl paramethoxy diphenyl sulphide,

This was obtained as a colorless crystalline compound melting at 45-46 and boiling at 181-1851. C. at 4 mm.

Dealkylation: The paramethyl paramethoxy diphenyl sulphide is then subjected to dealkylation by heating, for example, with hydrobromic acid in glacial acetic acid solution at a temperature of about to C. for a suilicient period of time, e. g., about eight hours, using about 1 to 2 mols of hydrobromic acid for each mole of the paramethyl paramethoxy diphenyl sulphide.

Excess of hydrobromic acid and acetic acid is then driven off and sodium hydroxide solution added. The alkaline solution is then heated at steam bath temperature to hydrolyze any acetylated product formed during the dealkylation process and finally extracted with ether to remove any of the unaltered alkylated product. The alkaline solution is then acidified and the liberated phenol extracted with ether. The ether extractflis dried, e. g., with calcium chloride, the ether distilled off, and the paramethyl parahydroxy diphenyl sulphide is then fractionally distilled under diminished pressure. The boiling point of paramethyl parahydroxy diphenyl sulphide is 178-180 at 3 mm. The compound melts at 6768 C.

The new paramethyl parahydroxy diphenyl sulphide has valuable germicidal properties and can be readily produced in a state of high purity I such that its germicidal properties can be taken 

